Pivaloyl-L-phenylalanine → (2S)-6-[[(2S)-2-(2,2-dimethylpropanoylamino)-3-phenyl-propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 396894Notes

Reaction equation

HRID 396894 reaction equation
[CH2:1]([N:5]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1)(=[O:34])=[O:33])[C@H:6]([C:29]([OH:31])=[O:30])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](OCC1C2C=CC=CC=2C2C1=CC=CC=2)=[O:13])[CH:2]([CH3:4])[CH3:3].[C:42]([NH:48][C@H:49](C(O)=O)[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44]>>[CH3:41][C:38]1[CH:37]=[CH:36][C:35]([S:32]([N:5]([C@H:6]([C:29]([OH:31])=[O:30])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C@@H:49]([NH:48][C:42]([C:43]([CH3:46])([CH3:45])[CH3:44])=[O:47])[CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:13])[CH2:1][CH:2]([CH3:4])[CH3:3])(=[O:34])=[O:33])=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 914376Pivaloyl-L-phenylalanineHCID 3013742(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Product 1

HCID 508575(2S)-6-[[(2S)-2-(2,2-dimethylpropanoylamino)-3-phenyl-propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Procedure

The title compound was prepared from solid phase bound Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-Nε-(9-fluorenylmethoxycarbonyl)-L-lysine as described in general procedure Bb using Nα-pivaloyl-L-phenylalanine (300 mg, 1.2 mmol). The final product was purified by preparative HPLC to yield 49 mg (66%) of the desired material.

Workup

  1. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-4cbe3f526a5744bd9a612716db8e3352
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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